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VINCAT SIGNED

A Unified Approach to Redox-Neutral C-C Couplings: Exploiting Vinyl Cation Rearrangements

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EC-Contrib. €

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Project "VINCAT" data sheet

The following table provides information about the project.

Coordinator
UNIVERSITAT WIEN 

Organization address
address: UNIVERSITATSRING 1
city: WIEN
postcode: 1010
website: www.univie.ac.at

contact info
title: n.a.
name: n.a.
surname: n.a.
function: n.a.
email: n.a.
telephone: n.a.
fax: n.a.

 Coordinator Country Austria [AT]
 Total cost 1˙940˙025 €
 EC max contribution 1˙940˙025 € (100%)
 Programme 1. H2020-EU.1.1. (EXCELLENT SCIENCE - European Research Council (ERC))
 Code Call ERC-2015-CoG
 Funding Scheme ERC-COG
 Starting year 2017
 Duration (year-month-day) from 2017-01-01   to  2021-12-31

 Partnership

Take a look of project's partnership.

# participants  country  role  EC contrib. [€] 
1    UNIVERSITAT WIEN AT (WIEN) coordinator 1˙940˙025.00

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 Project objective

The preparation of complex molecular architectures employing multi-component reactions where the number of bond-forming events is maximised is a central goal of the discipline of Organic Synthesis. The contemporary, pressing need for sustainable chemical reactions has raised the demand for novel reaction families that explore the concept of redox-neutrality and proceed with the generation of minimal waste. In this proposal, I present a unified and conceptually novel approach to atom-economical C-C bond formation in challenging contexts without the need for transition metal promoters or reagents. To this end, I propose the innovative harvesting of the potential of vinyl cation intermediates as platforms for the deployment of nucleophilic entities capable of orchestrating rearrangement reactions. The combination of such high-energy intermediates, generated under mild conditions, with the power of carefully designed rearrangements leads to an array of useful new transformations. Furthermore, the very high atom-economy and simplicity of these reactions renders them not only sustainable and environmentally friendly but also highly appealing for large-scale applications. Additional approaches to enantioselective synthesis further enhance the methods proposed. The paradigm proposed herein for the exploitation of vinyl cations will also open up new vistas in the centuries-old aldol reaction and in amination chemistry. This showcases the vast potential of these simple principles of chemical reactivity. The myriad of new reactions and new product families made possible by VINCAT will decisively enrich the toolbox of the synthetic practitioner.

 Publications

year authors and title journal last update
List of publications.
2018 Pauline Adler, Amandine Pons, Jing Li, Jörg Heider, Bogdan R. Brutiu, Nuno Maulide
Chemoselektive Aktivierung von Diethylphosphonaten: modulare Synthese von biologisch relevanten phosphonylierten Grundgerüsten
published pages: 13514-13518, ISSN: 0044-8249, DOI: 10.1002/ange.201806343
Angewandte Chemie 130/40 2020-01-30
2017 Giovanni Di Mauro, Boris Maryasin, Daniel Kaiser, Saad Shaaban, Leticia González, Nuno Maulide
Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles
published pages: 3815-3818, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.7b01678
Organic Letters 19/14 2019-06-06
2018 Daniel H. O\' Donovan, Paul Aillard, Martin Berger, Aurélien de la Torre, Desislava Petkova, Christian Knittl-Frank, Danny Geerdink, Marcel Kaiser, Nuno Maulide
C−H Activation Enables a Concise Total Synthesis of Quinine and Analogues with Enhanced Antimalarial Activity
published pages: 10737-10741, ISSN: 1433-7851, DOI: 10.1002/anie.201804551
Angewandte Chemie International Edition 57/33 2019-06-06
2018 Boris Maryasin, Philipp Marquetand, Nuno Maulide
Machine Learning for Organic Synthesis: Are Robots Replacing Chemists?
published pages: 6978-6980, ISSN: 1433-7851, DOI: 10.1002/anie.201803562
Angewandte Chemie International Edition 57/24 2019-06-06
2017 Daniel Kaiser, Christopher J. Teskey, Pauline Adler, Nuno Maulide
Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides
published pages: 16040-16043, ISSN: 0002-7863, DOI: 10.1021/jacs.7b08813
Journal of the American Chemical Society 139/45 2019-06-06
2018 James D. Neuhaus, Adriano Bauer, Alexandre Pinto, Nuno Maulide
A Catalytic Cross-Olefination of Diazo Compounds with Sulfoxonium Ylides
published pages: 16215-16218, ISSN: 1433-7851, DOI: 10.1002/anie.201809934
Angewandte Chemie International Edition 57/49 2019-06-06
2018 Alexandre Pinto, Daniel Kaiser, Boris Maryasin, Giovanni Di Mauro, Leticia González, Nuno Maulide
Hydrative Aminoxylation of Ynamides: One Reaction, Two Mechanisms
published pages: 2515-2519, ISSN: 0947-6539, DOI: 10.1002/chem.201706063
Chemistry - A European Journal 24/10 2019-06-06
2018 Boris Maryasin, Dainis Kaldre, Renan Galaverna, Immo Klose, Stefan Ruider, Martina Drescher, Hanspeter Kählig, Leticia González, Marcos N. Eberlin, Igor D. Jurberg, Nuno Maulide
Unusual mechanisms in Claisen rearrangements: an ionic fragmentation leading to a meta -selective rearrangement
published pages: 4124-4131, ISSN: 2041-6520, DOI: 10.1039/c7sc04736c
Chemical Science 9/17 2019-06-06
2018 Dainis Kaldre, Immo Klose, Nuno Maulide
Stereodivergent synthesis of 1,4-dicarbonyls by traceless charge–accelerated sulfonium rearrangement
published pages: 664-667, ISSN: 0036-8075, DOI: 10.1126/science.aat5883
Science 361/6403 2019-06-06

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